3-Acylindoles via a one-pot, regioselective Friedel-Crafts reaction

被引:50
作者
Wynne, JH
Lloyd, CT
Jensen, SD
Boson, S
Stalick, WM [1 ]
机构
[1] George Mason Univ, Dept Chem, Fairfax, VA 22030 USA
[2] USN, Res Lab, Div Chem, Washington, DC 20375 USA
来源
SYNTHESIS-STUTTGART | 2004年 / 14期
关键词
indole; regioselectivity; Friedel-Crafts reactions; acylations;
D O I
10.1055/s-2004-831177
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Within we report a general one-pot high-yielding Friedel-Crafts acylation of indole using acid chlorides and diethylaluminum chloride in gram scale quantities. This general synthesis affords products that are easily isolated and require no complex purification procedures.
引用
收藏
页码:2277 / 2282
页数:6
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